Phosphole compound

Patent metadata

Field	Value
Publication number	US-11174389-B2
Application number	US-201716329151-A
Country	US
Kind code	B2
Filing date	Jul 24, 2017
Priority date	Aug 31, 2016
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

A phosphole compound represented by the formula(wherein Ar1 and Ar2 are the same or different, and represent an optionally substituted aromatic hydrocarbon ring or an optionally substituted heteroaromatic ring; Ar3 represents a divalent π-conjugated unit; R1 represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group; R2 and R3 are the same or different, and represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group; and Z represents a reactive group) can provide a fluorescent dye capable of maintaining a high fluorescence quantum yield irrespective of solvent polarity, and providing an improved fluorescence quantum yield and light resistance even in environments containing large amounts of water.

First claim

The invention claimed is:

1. A phosphole compound represented by formula (1):

wherein Ar 1 and Ar 2 are the same or different, and represent an aromatic hydrocarbon ring or a heteroaromatic ring, and Ar 1 and Ar 2 are optionally substituted;
Ar 3 represents a divalent π-conjugated unit;
R 1 represents an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, wherein R 1 is optionally substituted;
R 2 and R 3 are the same or different, and represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, wherein the alkyl group, the cycloalkyl group, the aryl group, or the heteroaryl group are optionally substituted; and
Z represents carboxy, alkoxycarbonyl, hydroxy, halogenated alkyl, isocyano, isothiacyano, or a group having a structure represented by one of formulas (2A) to (2E) at an end thereof:

wherein R 5 represents a hydrogen atom or a sulfo group, R 6 represents an alkyl group, and the bond indicated by a solid line and a dashed line represents a single bond or a double bond.

2. The phosphole compound according to claim 1 , wherein Ar 3 represents an alkenylene group, an alkynylene group, an arylene group, or an heteroarylene group, and Ar 3 is optionally substituted.

3. The phosphole compound according to claim 1 , which is represented by formula (1B):

wherein Ar 2 , Ar 3 , R 1 , R 2 , R 3 , and Z are as defined above, and Ar 4 represents an aromatic hydrocarbon ring, and Ar 4 is optionally substituted.

4. The phosphole compound according to claim 1 , wherein Z is carboxy or alkoxycarbonyl.

5. The phosphole compound according to claim 1 , wherein Z is a group having a structure represented by one of formulas (2A) to (2E) at an end thereof:

wherein R 5 represents a hydrogen atom or a sulfo group, R 6 represents an alkyl group, and the bond indicated by a solid line and a dashed line represents a single bond or a double bond.

6. A fluorescent dye comprising the phosphole compound according to claim 1 .

7. The fluorescent dye according to claim 6 , which is for stimulated emission depletion (STED) imaging.

8. A protein labeling agent comprising the phosphole compound according to claim 5 .

9. A protein labeling agent comprising a phosphole compound represented by formula (1):

wherein Ar 1 and Ar 2 are the same or different, and represent an optionally substituted aromatic hydrocarbon ring or an optionally substituted heteroaromatic ring;
Ar 3 represents a divalent π-conjugated unit;
R 1 represents alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group wherein R 1 is optionally substituted;
R 2 and R 3 are the same or different, and represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, wherein the alkyl group, the cycloalkyl group, the aryl group, or the heteroaryl group are optionally substituted; and
Z represents an amine reactive group or a thiol reactive group.

10. The protein labeling agent according to claim 9 , wherein Ar 3 represents an alkenylene group, an alkynylene group, an arylene group, or a heteroarylene group, and Ar 3 is optionally substituted.

11. The protein labeling agent according to claim 9 , which is represented by formula (1B):

wherein Ar 2 , Ar 3 , R 1 , R 2 , R 3 , and Z are as defined above, and Ar 4 represents an aromatic hydrocarbon ring, and Ar 4 is optionally substituted.

12. A stimulated emission depletion (STED) imaging method using the phosphole compound according to claim 1 .

13. A protein labeling kit comprising the phosphole compound according to claim 5 .

14. A protein labeling method comprising reacting a protein with the phosphole compound according to claim 5 .

15. A protein labeling kit comprising the protein labeling agent according to claim 9 .

16. A protein labeling method comprising reacting a protein with the protein labeling agent according to claim 9 .

Assignees

• Univ Nagoya Nat Univ Corp

Inventors

• Yamaguchi Shigehiro
• Naka Aiko
• Taki Masayasu
• Wang Chenguang

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F9/6568

  having phosphorus atoms as the only ring hetero atoms · CPC title

• A61K49/00 Primary

  Preparations for testing in vivo · CPC title

• G01N21/64

  Fluorescence; Phosphorescence · CPC title

• C09B57/00 Primary

  Other synthetic dyes of known constitution · CPC title